WO2012073995A1 - Heteroaromatic ring compound and pest control application thereof - Google Patents

Abstract

The present invention provides a novel compound having a control activity against a pest. The present invention relates to a heteroaromatic ring compound represented by formula (1) [In the formula, Het represents a 5-membered heterocycle indicated by a formula H1, H2, H3, H4 or H5 (In the formula, Y1, Y2, Y3, Z1, Z2 and Z3 represent the meaning described in Claims of the present application, and the mark "·" on the left side of the structural formula represents a position which binds to A.); J represents a t-butyl group, a trimethylsilyl group, or the like; L represents a single bond, or a C1-C3 alkylene group; A represents a single bond, or the like; G represents a hydrogen atom, a halogen atom, or the like; D represents -N= or -CH=; and m represents 0 or 1.], a production method therefor, and a pest control agent containing the heteroaromatic ring compound.

Description

Heteroaromatic compounds and their use for pest control

The present invention relates to a heteroaromatic ring compound and its use for pest control.

A compound having a pest control activity has been found and developed as an active ingredient of a pest control agent.

Patent Document 1 describes a compound having a thiazole ring and a pyridine ring in the molecule.

Patent Document 2 describes a compound having a pyrazole ring and a pyrimidine ring in the molecule.

International Publication WO2006 / 024642 Pamphlet International Publication WO2009 / 016460 Pamphlet

An object of the present invention is to provide a novel compound having a controlling activity against pests.

As a result of studying to find a compound having a control activity against pests, the present inventor found that the compound represented by the following formula (1) has a control effect on pests, and further studied. As a result, the present invention has been completed.

That is, the present invention is as follows.
[Term 1] Formula (1)

[Where,
Het is represented by the following formula H1, H2, H3, H4 or H5:

{Where,
Y ¹ represents —O—, —S— or —NE ² —, Y ² and Y ³ are the same or different and represent —CE ¹ ═ or —N═, and at least one of Y ² and Y ³ Are —CE ¹ ═, Z ¹ , Z ² and Z ³ are the same or different and represent —CE ¹ ═ or —N═ (where E ¹ has one or more halogen atoms) Represents a C1-C2 alkyl group, a hydrogen atom or a halogen atom, and E ² represents a C1-C2 alkyl group which may have one or more halogen atoms.) The mark represents the position where A is combined. } Represents a 5-membered heterocycle represented by
J is the following formula J1 or J2:

(Where
R ¹ and R ² are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
R ⁴ and R ⁵ are the same or different and each represents a methyl group or an ethyl group;
R ⁶ represents a hydrogen atom or a C1-C6 chain hydrocarbon group. ) Represents a group represented by
L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms,
A represents a single bond, —O—, or —S (O) _x — when Het is a group represented by the formula H1, H2, H3 or H5 (where x represents 0, 1 or 2). And represents a single bond when Het is a group represented by formula H4,
G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or the following formulas G1, G2, G3 or G4:

(Where
R ^a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T ¹ which may have one or more atoms or groups selected from <Group α>;
R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, —C (O) —T ² , —S (O) ₂ —. T ^{3 represents} a C3-C9 trialkylsilyl group or a cyclopropyl group,
R ^c represents a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, —C (O) —T ² or a cyclopropyl group;
z represents 0, 1 or 2;
R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, —C (O) —T ² , —S (O) ₂ —. It represents T ³ or cyclopropyl group,
R ^e represents a C1-C6 chain hydrocarbon group, hydrogen atom or cyclopropyl group which may have one or more atoms or groups selected from <Group β>;
T ¹ has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, a hydroxyl group, an amino group, a hydrogen atom or a cyclopropyl group,
T ² has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, an amino group, a hydrogen atom or a cyclopropyl group,
T ³ represents a C1-C6 alkyl group which may have one or more halogen atoms. ) Represents a group represented by
D represents —N═ or —CH═,
m represents 0 or 1;
<Group α>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms A group consisting of an amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, a C3-C9 trialkylsilyl group, and a cyclopropyl group;
<Group β>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms An amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a phenyl group (the phenyl group is one selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group) And a group consisting of a halogen atom, a cyano group, a C3-C9 trialkylsilyl group, and a cyclopropyl group.

However, the compounds corresponding to the following (1) to (6) are excluded:
(1) Het is a group represented by the formula H1, Y ¹ is —S—, Y ² and Y ³ are —CH═, A is —O—, L is a single bond, A compound in which J is a group represented by formula J1, R ¹ , R ² and R ³ are all methyl groups, G is a hydrogen atom, D is —CH═ and m is 0 ,
(2) Het is a group represented by the formula H1, Y ¹ is —O—, Y ² and Y ³ are —CH═, A and L are single bonds, and J is represented by the formula J2. A compound in which R ⁴ , R ⁵ and R ⁶ are all methyl groups, G is a hydrogen atom, D is —CH═, and m is 0,
(3) Het is a group represented by the formula H3, Y ¹ is —S—, Y ² is —N═, Y ³ is —CH═, A and L are single bonds, A compound in which J is a group represented by formula J1, R ⁴ , R ⁵ and R ⁶ are all methyl groups, G is a hydrogen atom, D is —CH═ and m is 0 ,
(4) Het is a group represented by the formula H4, Z ¹ is —CH═, Z ² is —N═, and Z ³ is —CI═ (where I is an iodine atom) .), A and L are single bonds, J is a group represented by the formula J1, R ¹ and R ² are both methyl groups, R ³ is a hydrogen atom, and G is a hydrogen atom. A compound in which D is -N = and m is 0,
(5) Het is a group represented by the formula H4, Z ¹ is —N═, Z ² and Z ³ are —CH═, A and L are single bonds, and J is represented by the formula J1. R ¹ and R ² are both methyl groups, R ³ is a hydrogen atom or a methyl group, G is a hydrogen atom, D is —CH═ or —N═, a compound in which m is 0, and (6) Het is a group represented by the formula H5, Z ¹ is —N═, Z ² is —C (CH ₃ ) ═, and Z ³ is —CH═. A is —O—, L is a single bond, J is a group represented by the formula J1, R ¹ and R ² are both methyl groups, and R ³ is a hydrogen atom. A compound in which G is a hydrogen atom, D is —CH═, and m is 0. ]
A heteroaromatic ring compound represented by the following (hereinafter referred to as the present compound).
[Item 2] The heteroaromatic ring compound according to [Item 1], wherein Het is a group represented by the formula H1.
[Claim 3] The heteroaromatic ring compound according to [Claim 2], wherein Y ¹ is —S— or —O—.
[Item 4] The heteroaromatic ring compound according to [Item 2], wherein Y ¹ is —S—.
[Claim 5] The heteroaromatic ring compound according to [Claim 1], wherein Het is a group represented by H1, Formula H2 or H3, and Y ¹ is -S-.
[Item 6] The heteroaromatic ring compound according to [Item 1], wherein Het is a group represented by the formula H4.
[Term 7] Z ¹ is -N =, Z ² is -CE ¹ =, and Z ³ is -CE ¹ = or -N =, or Z ¹ is -CE ¹ = The heteroaromatic ring compound according to [Item 6], wherein Z ² is —N═, and Z ³ is —CE ¹ ═.
[Item 8] Z ¹ is -N = and Z ² and Z ³ are the same or different -CE ¹ =, or Z ² is -N = and Z ¹ and Z ³ are the same or The heteroaromatic ring compound according to item 7 wherein -CE ¹ = is different.
[Item 9] The heteroaromatic ring compound according to [Item 6], wherein Z ¹ and Z ³ are —N═, and Z ² is —CE ¹ ═.
[Item 10] The heteroaromatic ring compound according to [Item 1], wherein Het is a group represented by the formula H5.
[Term 11] Z ¹ is -N =, Z ² is -CE ¹ = and Z ³ is -CE ¹ = or -N =, or Z ¹ is -CE ¹ = The heteroaromatic ring compound according to Item 10, wherein Z ² is —N═ and Z ³ is —CE ¹ ═.
[Term 12] Z ¹ is -N = and Z ² and Z ³ are the same or different -CE ¹ =, or Z ² is -N = and Z ¹ and Z ³ are the same or The heteroaromatic ring compound according to [Item 11], wherein -CE ¹ = is different.
[Claim 13] The heteroaromatic ring compound according to [Claim 10], wherein Z ¹ and Z ³ are —N═, and Z ² is —CE ¹ ═.
[Item 14] A pest control agent comprising the heteroaromatic ring compound according to any one of [Item 1] to [Item 13] and an inert carrier.
[Item 15] Use of the heteroaromatic ring compound according to any one of [Item 1] to [Item 13] for controlling pests.
[Item 16] A method for controlling pests comprising a step of applying an effective amount of the heteroaromatic ring compound according to any one of [Item 1] to [Item 13] to a pest or a habitat of the pest.

The compound of the present invention is useful for controlling pests.

The terms used in this specification will be described below with examples.

In the compound of the present invention, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the compound of the present invention, examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” represented by E ¹ include a methyl group, an ethyl group, a trifluoromethyl group, and a difluoromethyl group. Etc.

In the compounds of the present invention, examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” represented by E ² include a methyl group, an ethyl group, and 2,2,2-trifluoroethyl. Group, and a 2,2-difluoroethyl group.

In the compound of the present invention, examples of the “C1-C3 alkyl group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a trifluoromethyl group.

Examples of the “C1-C6 alkyl group optionally having one or more halogen atoms” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a sec-butyl group. , Tert-butyl group, pentyl group, hexyl group and trifluoromethyl group.

In the compounds of the present invention, examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 2 , C1-C6 alkyl groups such as 2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group and hexyl group;
Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group C2-C6 alkenyl group such as ethynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3,3-dimethyl-1-butynyl group, 1-pentynyl group and 1-hexynyl group And C2-C6 alkynyl groups such as

Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, sec 1 such as -butyl group, tert-butyl group, pentyl group, 2,2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group hexyl group and trifluoromethyl group A C1-C6 alkyl group optionally having one or more halogen atoms;
Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group A C2-C6 alkenyl group optionally having one or more halogen atoms such as a C2-C6 alkenyl group such as 2,2-difluorovinyl group, etc .; and an ethynyl group, a propargyl group, a 1-butynyl group, 2- C2 which may have one or more halogen atoms such as butynyl group, 3-butynyl group, 3,3-dimethyl-1-butynyl group, 1-pentynyl group, 1-hexynyl group and 2-chloroethynyl group -C6 alkynyl group can be mentioned.

In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <group α>” include a methyl group, an ethyl group, a propyl group, and an isopropyl group. A C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group and tert-butyl group;
C1- having one or more atoms or groups selected from <Group α> such as trifluoromethyl group, cyanomethyl group, cyclopropylmethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group and methylthiomethyl group A C6 alkyl group;
One or more atoms selected from <Group α> such as vinyl group, isopropenyl group, 1-propenyl group, 2-methyl-1-propenyl group, 2,2-dichlorovinyl group and 2,2-difluorovinyl group Or a C2-C6 alkenyl group which may have a group; and <group α> such as an ethynyl group, a 1-propynyl group, a 2-chloroethynyl group, a 2-fluoroethynyl group and a 2- (trimethylsilyl) ethynyl group And C2-C6 alkynyl group which may have one or more selected atoms or groups.

In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <group β>” include a methyl group, an ethyl group, a propyl group, an isopropyl group. A C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group and tert-butyl group;
Difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,1-trifluoro-2-propyl group, cyanomethyl group 1-cyanoethyl group, cyclopropylmethyl group, 1- (cyclopropyl) ethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, methylthiomethyl group, methylsulfinylmethyl group, methyl Sulfonylmethyl group, 2- (methylthio) ethyl group, 2- (methylsulfinyl) ethyl group, 2- (methylsulfonyl) ethyl group, 2- (methylamino) ethyl group, 2- (dimethylamino) ethyl group, benzyl group 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-nitrobenzyl group, etc. C1-C6 alkyl group having one or more atoms or groups selected from <group beta>;
A C3-C6 alkenyl group optionally having one or more atoms or groups selected from <Group β> such as 2-propenyl group, 2-butenyl group and 3-methyl-2-butenyl group; and a propargyl group And a C2-C6 alkynyl group optionally having one or more atoms or groups selected from <Group β> such as 2-butynyl group and 3-butynyl group.

Examples of the “C1-C3 alkylene group optionally having one or more halogen atoms” in the compounds of the present invention include —CH ₂ —, —CHCl—, —CHF—, —CF ₂ —, —CH ₂ CH ₂ -and -CH ₂ CH ₂ CH ₂ -are mentioned.

In the compounds of the present invention, examples of the “C3-C9 trialkylsilyl group” include a trimethylsilyl group, a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, and a triisopropylsilyl group.

Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group. Group, tert-butoxy group, 2,2,2-trichloroethoxy group and 2,2,2-trifluoroethoxy group.

In the compounds of the present invention, examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” include, for example, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutyl An amino group, a sec-butylamino group, a tert-butylamino group and a 2,2,2-trifluoroethylamino group can be mentioned.

Examples of the “C2-C12 dialkylamino group optionally having one or more halogen atoms” in the compound of the present invention include N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl group. Amino group, N, N-dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methyl An amino group and an N-methyl-N- (2,2,2-trifluoroethyl) amino group can be mentioned.

Examples of the “C1-C4 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group. Group, tert-butoxy group and 2,2,2-trifluoroethoxy group.

In the compound of the present invention, examples of the “C1-C4 alkylthio group optionally having one or more halogen atoms” include, for example, methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec- Examples thereof include a butylthio group, a tert-butylthio group and a 2,2,2-trifluoroethylthio group.

Examples of the “C1-C4 alkylsulfinyl group optionally having one or more halogen atoms” in the compounds of the present invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutyl group. Examples thereof include a sulfinyl group, a sec-butylsulfinyl group, a tert-butylsulfinyl group, and a 2,2,2-trifluoroethylsulfinyl group.

In the compound of the present invention, examples of the “C1-C4 alkylsulfonyl group optionally having one or more halogen atoms” include, for example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutyl Examples include a sulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, and a 2,2,2-trifluoroethylsulfonyl group.

In the compounds of the present invention, examples of the “C1-C4 alkylamino group optionally having one or more halogen atoms” include, for example, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutyl An amino group, a sec-butylamino group, a tert-butylamino group and a 2,2,2-trifluoroethylamino group can be mentioned.

Examples of the “C2-C8 dialkylamino group optionally having one or more halogen atoms” in the compounds of the present invention include N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl group. Amino group, N, N-dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methyl An amino group and an N-methyl-N- (2,2,2-trifluoroethyl) amino group can be mentioned.

In the compound of the present invention, the “phenyl group (the phenyl group may have one or more groups selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group)” is, for example, a phenyl group 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 4-nitrophenyl group, 2-nitrophenyl group, 4-chlorophenyl group, 2-chlorophenyl group, 2,6-dichlorophenyl group and 4-methylphenyl group. Can be mentioned.
In the compound of the present invention, when the 5-membered heteroaromatic ring represented by Het contains two or more —CE ¹ ═, each E ¹ group may be the same or different.

Specific examples of the 5-membered heteroaromatic ring represented by the formula H1 in the compound of the present invention are shown below. In the following, the “•” mark on the left side of the structural formula represents the position where A is combined.

(In the formula, E ¹ and E ² represent the same meaning as described above.)
Specific examples of the 5-membered heteroaromatic ring represented by the formula H2 in the compound of the present invention are shown below.

(In the formula, E ¹ and E ² represent the same meaning as described above.)
Specific examples of the 5-membered heteroaromatic ring represented by the formula H3 in the compound of the present invention are shown below.

(In the formula, E ¹ and E ² represent the same meaning as described above.)
Specific examples of the 5-membered heteroaromatic ring represented by the formula H4 in the compound of the present invention are shown below.

 

 

(Wherein E ¹ represents the same meaning as described above.)
Specific examples of the 5-membered heteroaromatic ring represented by the formula H5 in the compound of the present invention are shown below.

(Wherein E ¹ represents the same meaning as described above.)
As this invention compound, the following hetero aromatic ring compounds are mentioned, for example.
[Aspect A]
In the formula (1), compounds wherein Het is a group represented by the formula H1, H2 or H3.
[Aspect B]
In the formula (1), compounds wherein Het is a group represented by the formula H1, H2 or H3 and Y ¹ is —O— or —S—.
[Aspect C]
In the formula (1), compounds wherein Het is a group represented by the formula H1, H2 or H3 and Y ¹ is —S—.
[Aspect D]
In the formula (1), compounds wherein Het is a group represented by the formula H1.
[Aspect E]
In the formula (1), compounds wherein Het is a group represented by the formula H1 and Y ¹ is —O— or —S—.
[Aspect F]
In the formula (1), compounds wherein Het is a group represented by the formula H1 and Y ¹ is —S—.
[Aspect G]
In the formula (1), compounds wherein Het is a group represented by formula H1, Y ¹ is —S— and Y ² and Y ³ are —CE ¹ ═.
[Aspect H]
In the formula (1), compounds wherein Het is a group represented by formula H4.
[Aspect I]
In the formula (J), compounds wherein Het is a group represented by formula H4, one or two of Z ¹ , Z ² and Z ³ is —N═, and the others are —CE ¹ ═.
[Aspect J]
In the formula (1), compounds wherein Het is a group represented by the formula H4, ^one of Z ¹ , Z ² and Z ³ is —N═ and the other is —CE ¹ =.
[Aspect K]
In the formula (1), Het is a group represented by the formula H4, Z ¹ is -N =, Z ² is -CE ¹ =, and Z ³ is -CE ¹ = or -N = Or a compound wherein Z ¹ is —CE ¹ ═, Z ² is —N═ and Z ³ is —CE ¹ ═.
[Aspect L]
In the formula (1), compounds wherein Het is a group represented by the formula H4, Z ¹ is -N =, Z ² is -CE ¹ = and Z ³ is -CE ¹ = or -N = .
[Aspect M]
In the formula (1), Het is a group represented by the formula H4, ^one of Z ¹ and Z ² is —N═, the other is —CE ¹ =, and Z ³ is —CE ¹ = A compound.
[Aspect N]
In the formula (1), compounds wherein Het is a group represented by the formula H4, Z ¹ is —N═ and Z ² and Z ³ are the same or different and CE ¹ =.
[Aspect O]
In the formula (1), compounds wherein Het is a group represented by formula H4, Z ² is —N═ and Z ¹ and Z ³ are the same or different and CE ¹ =.
[Aspect P]
In the formula (1), compounds wherein Het is a group represented by the formula H5.
[Aspect Q]
In the formula (1), compounds wherein Het is a group represented by the formula H5, one or two of Z ¹ , Z ² and Z ³ are —N═, and the others are —CE ¹ ═.
[Aspect R]
In the formula (1), compounds wherein Het is a group represented by the formula H5, ^one of Z ¹ , Z ² and Z ³ is —N═ and the other is —CE ¹ =.
[Aspect S]
In the formula (1), Het is a group represented by the formula H5, Z ¹ is -N =, Z ² is -CE ¹ =, and Z ³ is -CE ¹ = or -N = Or a compound wherein Z ¹ is —CE ¹ ═, Z ² is —N═ and Z ³ is —CE ¹ ═.
[Aspect T]
In the formula (1), compounds wherein Het is a group represented by the formula H5, Z ¹ is -N =, Z ² is -CE ¹ = and Z ³ is -CE ¹ = or -N = .
[Aspect U]
In the formula (1), Het is a group represented by the formula H5, ^one of Z ¹ and Z ² is —N═, the other is —CE ¹ =, and Z ³ is —CE ¹ = A compound.
[Aspect V]
In the formula (1), compounds wherein Het is a group represented by the formula H5, Z ¹ is —N═, Z ² and Z ³ are the same or different and CE ¹ ═.
[Aspect W]
In the formula (1), compounds wherein Het is a group represented by the formula H5, Z ² is —N═, Z ¹ and Z ³ are the same or different and CE ¹ =.
[Aspect X]
The heteroaromatic ring compound according to [Item 1] represented by the following formula:

(In the formula, n represents 0, 1 or 2, p represents 0, 1, 2 or 3, and other symbols have the same meaning as described above.)
[Aspect Y]
The heteroaromatic ring compound according to [Item 1] represented by the following formula:

 

 

(In the formula, each symbol represents the same meaning as described above.)
[Aspect Z]
The heteroaromatic ring compound according to [Item 1] represented by the following formula:

(In the formula, each symbol represents the same meaning as described above.)
Moreover, as this invention compound, the following hetero aromatic ring compounds are also mentioned, for example.
[Aspect 1] to [Aspect 23]
The heteroaromatic ring compound according to any one of [Item 1] and [Aspect A] to [Aspect Z], wherein G is [Aspect 1] to [Aspect 23] described in [Table 1]. For example, [Aspect 1] is “In Formula (1), G is a hydrogen atom, a halogen atom, a group represented by Formulas G1, G2, G3, or G4 [Item 1] and [Aspect A] to The heteroaromatic ring compound according to any one of [Aspect Z].

In addition, examples of the compound of the present invention include the following heteroaromatic ring compounds.

The compound according to any one of [Item 1], [Aspect A] to [Aspect Z], and [Aspect 1] to [Aspect 23], wherein D is —CH═ in formula (1);
The compound according to any one of [Item 1], [Aspect A] to [Aspect Z], and [Aspect 1] to [Aspect 23], wherein D is —N═ in formula (1);
In the formula (1), L is a single bond or —CH ₂ —, A is a single bond or —O—, and J is a group represented by the formula J1 or J2. ] To [Aspect Z] and [Aspect 1] to [Aspect 23];
In the formula (1), L is a single bond or —CH ₂ —, A is a single bond or —O—, and J is a group represented by the formula J1 (R ¹ and R ² are both methyl groups) , R ³ is a hydrogen atom, a methyl group, or an ethyl group.) Or a group represented by formula J2 (R ⁴ , R ^5, and R ⁶ are all methyl groups), [Claim 1], The compound according to any one of [Aspect A] to [Aspect Z] and [Aspect 1] to [Aspect 23];
In the formula (1), L is —CH ₂ —, A is a single bond, J is a group represented by the formula J1 (R ¹ and R ² are both methyl groups, R ³ is a hydrogen atom, A methyl group or an ethyl group) or a group represented by formula J2 (wherein R ⁴ , R ⁵ and R ⁶ are all methyl groups), [Item 1], [Aspect A] to [Aspect Z] and the compound according to any one of [Aspect 1] to [Aspect 23];
The compound according to any one of [Item 1], [Aspect A] to [Aspect Z], and [Aspect 1] to [Aspect 23], wherein JLA is a neopentyl group in Formula (1);
In the formula (1), G is a hydrogen atom or a halogen atom,
G is a group represented by the formula G1, and R ^a is ^a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group α>;
G is a group represented by the formula G2, and R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>,
G is a group represented by the formula G3, and R ^c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, or ,
G is a group represented by the formula G4, R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, and R ^e Is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group β> [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
In Formula (1), G is a halogen atom,
G is a group represented by the formula G1, and R ^a is ^a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group α>;
G is a group represented by the formula G2, and R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>,
G is a group represented by the formula G3, and R ^c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, or ,
G is a group represented by the formula G4, R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, and R ^e Is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group β> [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
In the formula (1), G is a group represented by the formula G1, and R ^a may have one or more atoms or groups selected from <Group α>. Or
G is a group represented by the formula G2, and R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>,
G is a group represented by the formula G3, and R ^c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, or ,
G is a group represented by the formula G4, R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, and R ^e Is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group β> [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
In the formula (1), G is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2, 2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N -Dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-tri Fluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-tri Ruoroechiru) an amino group compound according to any one of [claim 1] and [Embodiment A] ~ [aspect Z];
In the formula (1), G is fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-tri Fluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl Amino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) Amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroe A compound according to any one of the Le) is an amino group [claim 1] and [Embodiment A] ~ [aspect Z];
In the formula (1), G is methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group , Propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N- Methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroethyl) amino group [Claim 1] and A compound according to any one of embodiments A] ~ [aspect Z];
C1-C6 chain hydrocarbon in which G is a group represented by formula G2 and R ^b may have one or more atoms or groups selected from <Group β> in formula (1) A C1-C6 chain hydrocarbon which is a group, or G is a group represented by the formula G3, and R ^c may have one or more atoms or groups selected from <Group β> The heterocyclic compound according to any one of [Item 1] and [Aspect A] to [Aspect Z], which is a group;
In the formula (1), G is methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, or 2,2, The compound according to any one of [Item 1] and [Aspect A] to [Aspect Z], which is a 2-trifluoroethylthio group;
In the formula (1), G is a group represented by the formula G1, and R ^a may have one or more atoms or groups selected from <Group α>. Group or
G is a group represented by the formula G4, R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, and R ^e Is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group β> [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
In the formula (1), G is methyl group, ethyl group, propyl group, isopropyl group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N. -Methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group , N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroethyl) amino group [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
In the formula (1), G is a group represented by the formula G1, and R ^a may have one or more atoms or groups selected from <Group α>. [Claim 1] which is a group and the compound according to any one of [Aspect A] to [Aspect Z];
In the formula (1), G is a methyl group, an ethyl group, a propyl group or an isopropyl group [Claim 1] and the compound according to any one of [Aspect A] to [Aspect Z];
C1-C6 chain hydrocarbon in which G is a group represented by formula G2 and R ^b may have one or more atoms or groups selected from <Group β> in formula (1) [Claim 1] which is a group and the compound according to any one of [Aspect A] to [Aspect Z];
In the formula (1), any one of [Claim 1] and [Aspect A] to [Aspect Z], wherein G is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, or a 2,2,2-trifluoroethoxy group A compound according to claim 1;
In the formula (1), G is a group represented by the formula G3, and R ^c may have one or more atoms or groups selected from <Group β>. The compound according to any one of [Item 1] and [Aspect A] to [Aspect Z], which is a group;
In the formula (1), G is a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, or a 2,2,2-trifluoroethylthio group. Any one of the compounds;
In the formula (1), G is a group represented by the formula G4, and R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>. And R ^e is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group β> [Claim 1] and [Aspect A ] To [Aspect Z]
In the formula (1), G is N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propyl. Amino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group The compound according to any one of [Item 1] and [Aspect A] to [Aspect Z], which is an N-isopropylamino group or an N- (2,2,2-trifluoroethyl) amino group.

Next, a method for producing the compound of the present invention will be described.

The compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 9).

(Production method 1)
Among the compounds of the present invention, compounds in which Het is a group represented by the formulas H1, H2, H3 and H4 can be produced, for example, according to the following scheme.

[Represents wherein, J, L, A, D and G and m are as defined above, Het1 represents a group of the formula H1, H2, H3 or H4, Lg ¹ is a chlorine atom, a bromine atom, It represents a leaving group such as an iodine atom or a trifluoromethanesulfonyloxy group, Lg ² represents a B (OH) ₂ group or a B (OR ^f ) ₂ group (wherein R ^f may be the same or different) , A C1-C6 alkyl group, and two R ^f can be bonded to form a —CH ₂ CH ₂ — group or a —C (CH ₃ ) ₂ C (CH ₃ ) ₂ — group. To express. ]

-Production of (1a) The compound of the present invention can produce compound (1a) by reacting compound (2) with the compound represented by formula (3) in the presence of a solvent, a catalyst and a base. .

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile, and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, water, and mixtures thereof.

Examples of the catalyst used in the reaction include palladium catalysts such as tetrakis (triphenylphosphine) palladium and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium methylene chloride complex. The amount of the catalyst used is in the range of 0.0001 to 0.1 times mol for 1 mol of compound (2).

Examples of the base used in the reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, potassium tert-butoxide, potassium phosphate, and organic acid salts such as sodium acetate and potassium acetate. Is mentioned. The amount of the base used is in the range of 0.5 to 10 times mol per mol of compound (2).

Compound (3) is usually used at a ratio of 1 mol per 1 mol of compound (2), but can be appropriately changed.

The reaction temperature in the reaction is usually in the range of 20 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.

The reaction is preferably performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.

After completion of the reaction, the compound (1a) can be isolated by carrying out ordinary post-treatment operations.

(Production method 2)
Among the compounds of the present invention, a compound in which Het is a group represented by the formula H4 can be produced, for example, according to the following scheme.

[Wherein, J, L, D, G, Z ¹ , Z ² , Z ³ and m represent the same meaning as described above, and Lg ³ represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, paratoluene. It represents a leaving group such as a sulfonyloxy group or a trifluoromethanesulfonyloxy group. ]

-Production of (1b) The compound (1b) of the present invention can be produced by reacting the compound (4) and the compound (5) in the presence of a base.

The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, chlorides, and the like. Examples thereof include halogenated hydrocarbons such as methylene and chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in a proportion of 1 mol to 10 mol with respect to compound (4).

Compound (5) is usually used at a ratio of 1 mol per 1 mol of compound (4), but can be appropriately changed.

The reaction temperature in the reaction between the compound (4) and the compound (5) is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (1b) of the present invention can be isolated by performing ordinary post-treatment operations.

(Production method 3)
Among the compounds of the present invention, a compound in which Het is a group represented by the formula H5 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, D, G, Z ¹ , Z ² , Z ³ and m represent the same meaning as described above, and Lg ⁴ represents a leaving group such as a fluorine atom, a chlorine atom or a bromine atom. To express. ]

-Production of (1c) The compound (1c) of the present invention can be produced by reacting the compound (6) and the compound (7) in the presence of a base.

The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, chlorides, and the like. Examples thereof include halogenated hydrocarbons such as methylene and chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in a proportion of 1 mol to 10 mol with respect to compound (6).

Compound (7) is usually used in a ratio of 1 mol per 1 mol of compound (6), but can be appropriately changed.

The reaction temperature in the reaction of the compound (6) and the compound (7) is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations.

(Production Method 4)
Among the compounds of the present invention, compounds in which Het is a group represented by the formulas H1, H2, and H3 can be produced, for example, according to the following scheme.

[Wherein, J, L, D, G, Lg ² and m represent the same meaning as described above, Het2 represents a group represented by the formula H1, H2 or H3, and L ′ represents a single bond or one or more halogens. Represents a C1-C2 alkyl group which may have an atom; Lg ⁵ represents a leaving group such as a chlorine atom, a bromine atom or an iodine atom; R ^g represents a hydrogen atom, a methyl group, a methylthio group, a methoxy group, a phenyl group; Represents a group, a phenoxy group or an imidazolyl group. ]

・ (8) → (10)
Compound (10) can be produced by reacting compound (8) with an alkyllithium compound and then reacting the resulting reaction intermediate with an aldehyde represented by formula (9).

Two Lg ¹ of the compound (8) may be the same or different.

The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Is mentioned.

Examples of the alkyllithium compound used in the reaction include n-, sec- or tert-butyllithium, preferably n-butyllithium. The alkyllithium compound is usually used at a ratio of 1 mol per 1 mol of the compound (8), but can be appropriately changed.

The reaction temperature in the reaction between the compound (8) and the alkyl lithium compound is usually in the range of −78 ° C. to 0 ° C., and the reaction time is usually in the range of 1 hour from the instant.

Compound (9) is usually used at a ratio of 1 mol per 1 mol of compound (8), but can be appropriately changed.

The reaction temperature in the reaction between the reaction intermediate and compound (8) is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (10) can be isolated by pouring water or an aqueous ammonium chloride solution into the reaction mixture, extracting with an organic solvent, and performing a normal post-treatment operation.

・ (10) → (11)
This reaction can be produced by the production method of compound (1a) described in production method 1 or a method analogous thereto.

・ (11) → (12) → (1d)
The reaction can be prepared by a Barton-McCombie dehydroxylation reaction known to those skilled in the art.

(Production method 5)
Among the compounds of the present invention, a compound in which Het is a group represented by the formula H5 and D is —N═ can be produced, for example, according to the following scheme.

[Wherein, J, L, A, G, Lg ⁴ , Z ¹ , Z ² , Z ³ and m represent the same meaning as described above. ]

-Production of (14) Compound (14) can be produced by reacting compound (6) with dihalopyrimidine compound (13) in the presence of a base.

Two Lg ⁴ groups in the compound (13) may be different from each other, but a compound in which the two Lg ⁴ groups are both chlorine atoms is preferable.

The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, methylene chloride, and the like. Halogenated hydrocarbons such as chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (6).

Compound (13) is usually used at a ratio of 1 mol per 1 mol of compound (6), but can be appropriately changed.

The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.

The reaction time in the reaction is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (14) can be isolated by performing ordinary post-treatment operations.

・ (14) → (1e)
The compound (1e) of the present invention can be produced by dehalogenating the compound (14). Examples of the dehalogenation method include a catalytic hydrogen reduction reaction. The catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.

Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, esters such as ethyl acetate, carboxylic acids such as acetic acid, and water.

Also, a base or acid can be added as necessary. In this case, the molar ratio is usually 0.01 mol to 10 mol with respect to 1 mol of compound (14).

Examples of the base used in the reaction include magnesium oxide, sodium hydroxide, sodium acetate, and triethylamine. Examples of the acid include sulfuric acid and hydrochloric acid.

Examples of the catalyst used in the reaction include palladium on carbon.

In this reaction, the hydrogen pressure is usually 1 to 5 atm.

The reaction time in the reaction is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the present compound (1e) can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.

(Production method 6)
Among the compounds of the present invention, a compound in which G is a group represented by the formula G2 can be produced, for example, according to the following scheme.

[Wherein, J, L, A, Het, D, R ^b , Lg ³ and m represent the same meaning as described above, and R ^b1 has one or more atoms or groups selected from <Group β>. Represents an optionally substituted C1-C6 chain hydrocarbon group, and R ^b2 represents an OH-protecting group (for example, a methyl group, a methoxymethyl group, a benzyl group, etc.). ]

・ (1f) → (1g ′)
The compound (1g ′) of the present invention can be produced by reacting the compound (1f) of the present invention with R ^b1 OH in the presence of a base.

The reaction is usually performed in the presence of a solvent, but R ^b1 OH may be used in an amount of a solvent.

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile. Nitriles such as N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.

R ^b1 OH is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (1f) of the present invention.

The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the compound of the present invention (1g ′) can be isolated by performing a general post-treatment operation after the reaction.

・ (1i) → (1h)
The compound (1h) of the present invention can be produced by deprotecting the compound (1i) of the present invention.

Examples of the protecting group R ^b2 include a methyl group, a methoxymethyl group, and a benzyl group, which can be deprotected by methods known to those skilled in the art.

・ (1h) → (1g)
The compound (1g) of the present invention can be produced by reacting the compound (1h) of the present invention with R ^b Lg ^{3 in} the presence of a base.

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile. Nitriles such as N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide. Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (1h) of the present invention.

Present compound (1h) with respect to 1 mole, R ^b Lg ³ is used usually in a proportion of 1 mole, but may be appropriately changed.

The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually from 0.1 to 24 hours.

After completion of the reaction, the compound of the present invention (1 g) can be isolated by carrying out normal post-treatment operations after completion of the reaction.

In addition, this invention compound (1g) includes this invention compound (1g ').

(Production method 7)
Among the compounds of the present invention, a compound in which G is a group represented by the formula G3 can be produced according to the following scheme.

[Wherein, J, L, A, Het, D and m represent the same meaning as described above, and R ^c1 may have one or more atoms or groups selected from <Group β>. Represents a C6 chain hydrocarbon group. ]
The compound (1j) of the present invention can be produced by reacting the compound (1f) of the present invention with R ^c1 SH in the presence of a base.

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile. Nitriles such as N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.

R 1 ^C1 SH is usually used in a proportion of 1 to 10 mol and a base is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (1f) of the present invention.

The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually from 0.1 to 24 hours.

After completion of the reaction, the compound (1j) of the present invention can be isolated by performing ordinary post-treatment operations.

After completion of this reaction, the present compound (1j) is further subjected to an oxidation reaction known to those skilled in the art to convert -SR ^c1 in the present compound (1j) to -S (O) _z1 R ^c1 (in this case) , Z1 represents 1 or 2).

(Production method 8)
Among the compounds of the present invention, a compound in which G is a group represented by the formula G4 can be produced according to the following scheme.

[Wherein, J, L, A, Het, D, Lg ³ , R ^d , R ^e and m represent the same meaning as described above. ]

・ (1k) → (1l)
The compound (1l) of the present invention can be produced by reacting the compound (1k) of the present invention with R ^d Lg ^{3 in} the presence of a base.

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile. Nitriles such as N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide. Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is generally used in a ratio of 1 mol to 2 mol with respect to 1 mol of the compound (1k) of the present invention.

R ^e Lg ³ is usually used in a proportion of 1 mol per 1 mol of the compound (1k) of the present invention, but can be appropriately changed.

The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the compound of the present invention (1l) can be isolated by carrying out ordinary post-treatment operations.

・ (1l) → (1m)
Further, with respect to the present invention the compound (1l), by reacting R ^e Lg ² is prepared by an analogous procedure to the above, it can be produced the present invention compound (1 m).

When R ^d or R ^e is a primary or secondary alkyl group, the present compound (1k) or the present compound (1l) is reduced with an aldehyde or a ketone compound instead of the above method. This invention compound (1l) or this invention compound (1m) can also be manufactured by making it react in presence of an agent.

Examples of the reducing agent used in the reaction include sodium triacetoxyborohydride. Sodium triacetoxyborohydride is used in a ratio of 1 to 5 moles with respect to 1 mole of the compound (1k) or the compound (1l) of the present invention.

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane and chloroform, and the like. A mixture is mentioned. Moreover, it reacts by adding carboxylic acids, such as an acetic acid, as needed.

The aldehyde or ketone compound is usually used at a ratio of 1 mole per 1 mole of the compound (1k) or the compound (1l) of the present invention, but can be appropriately changed.

The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the compound of the present invention (1l) or the compound of the present invention (1m) can be isolated by performing ordinary post-treatment operations.

(Production method 9)
Among the compounds of the present invention, a compound in which m is 1 can be produced according to the following scheme.

[Wherein, J, L, A, Het, D and G represent the same meaning as described above. ]
The compound (1o) of the present invention can be produced by reacting the pyridine compound represented by the formula (1n) with an oxidizing agent.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent used in the reaction include halogenated hydrocarbons such as methylene chloride and chloroform, acetic acid, water, and mixtures thereof.

Examples of the oxidizing agent used in the reaction include peroxides of carboxylic acids such as 3-chloroperbenzoic acid, hydrogen peroxide water, and the like.

The oxidizing agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the compound (1n).

The reaction temperature of the reaction is usually in the range of −20 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (1o) of the present invention can be isolated by carrying out ordinary post-treatment operations.

Some of the intermediates used in the production of the active compound are commercially available or disclosed in known literature. The intermediate of the present invention can be produced, for example, by the following method.

(Intermediate production method 1)
Among the compounds of the present invention, Het is a group represented by the formula H4, and an intermediate (4a) of a compound in which Z ¹ , Z ² and Z ³ are —CE ¹ ═ is produced, for example, according to the following scheme be able to.

[Wherein, D, G, E ¹ and m represent the same meaning as described above. ]
Compound (4a) can be produced by reacting compound (15) with p-toluenesulfonyl isocyanide compound (16) in the presence of a base.

The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, chlorides, and the like. Examples thereof include halogenated hydrocarbons such as methylene and chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Examples of the base used in the reaction include sodium hydride, sodium tert-butoxide, potassium tert-butoxide, 1,8-diazabicyclo [5,4,0] undec-7-ene, n-butyllithium and the like. The base is usually used in a proportion of 1 mol to 10 mol with respect to compound (15).

The reaction can be performed in the presence of an additive (for example, a metal salt such as lithium bromide) as necessary.

The paratoluenesulfonyl isocyanide compound (16) is usually used at a ratio of 1 mole per 1 mole of the compound (15), but can be changed as appropriate.

The reaction temperature in the reaction of the compound (15) and the compound (16) is usually in the range of −78 ° C. to 30 ° C., and the reaction time is in the range of 0.1 hour to 24 hours.

After completion of the reaction, the compound (4a) can be isolated by performing a normal post-treatment operation.

(Intermediate production method 2)
Among the compounds of the present invention, Het is a group represented by the formula H4, Z ¹ is -N =, Z ² and Z ³ are -CE ¹ =, and the intermediate (4b) of the compound is, for example, It can be produced according to the scheme of

[Wherein, D, G, E ¹ and m represent the same meaning as described above, R ^h represents a C1-C6 alkyl group, and R ^h may be the same or different. ]

・ (17) → (19)
Compound (19) can be produced by reacting compound (17) with compound (18).

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile, and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof. Moreover, it can also be made to react by using an acetal compound represented by Formula (18) in excess without using a solvent. The amount thereof to be used is generally in the range of 1.0 mol to 10 mol with respect to 1 mol of compound (17).

The reaction temperature in the reaction of the compound (17) and the compound (18) is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (19) can be isolated by ordinary post-treatment operations.

・ (19) → (4b)
Compound (4b) can be produced by reacting compound (19) with hydrazine.

Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile, and the like. Nitriles, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.

Hydrazine is usually used in a ratio of 1 mol per 1 mol of compound (19), but can be changed as appropriate.

The reaction temperature in the reaction of the compound (19) with hydrazine is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (4b) can be isolated by carrying out a normal post-treatment operation.

(Intermediate production method 3)
Among the compounds of the present invention, an intermediate (4c) of a compound in which Het is a group represented by the formula H4, Z ¹ and Z ³ are —CE ¹ ═, and Z ² is —N═ is, for example, the following scheme Can be manufactured according to

[Wherein, D, G, E ¹ and m represent the same meaning as described above. ]

-Production of (4c) Compound (4c) can be produced from compound (19) described in Intermediate Production Method 2 by the production method of compound (4b) or a method analogous thereto.

(Intermediate production method 4)
Among the compounds of the present invention, an intermediate (4e) of a compound in which Het is a group represented by the formula H4 and Z ¹ , Z ² and Z ³ are —N═ can be produced, for example, according to the following scheme Can do.

[Wherein, D, G, E ¹ , R ^j and m represent the same meaning as described above. ]

・ (21) → (18)
This reaction can be produced by the production method of compound (18) from compound (17) described in Intermediate production method 2 or a method analogous thereto.

・ (22) → (4e)
Compound (4e) can be produced by reacting compound (22) with hydrazine.

Examples of the solvent used in the reaction include acetic acid.

The hydrazine compound is usually used at a ratio of 1 mole per 1 mole of the compound (22), but can be appropriately changed.

The reaction temperature in the reaction between the compound (22) and the hydrazine compound is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.

After completion of the reaction, the compound (4e) can be isolated by ordinary post-treatment operations.

Among the compounds of the present invention, there are also compounds capable of forming acid addition salts such as hydrochloride, nitrate, sulfate, hydrobromide, phosphate, carbonate, acetate, lactate, citrate, etc. To do. The production of these acid addition salts can also follow conventional methods, and the present invention also includes these acid addition salts.

Examples of pests for which the compounds of the present invention are effective include harmful arthropods such as harmful insects and harmful mites, linear animals and molluscs. Specific examples of such pests include the following.

Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypi), peach aphids (Myzus persicae), radish aphids (Brevicorine brassicae), aphid spiraecola, tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum pasid), citrus aphids (Topoptera citricidus), peach beetles Helmet beetle (Riptortus clavetus), spider helicopter (Leptocorisa chinensis), spider beetle (Eysarcoris parvus), winged beetle (Halyomorpha misista), and the like rodes vaporariorum), sweetpotato whitefly (Bemisia tabaci), mandarin orange whitefly (Dialeurodes citri), whiteflies such as mandarin orange spiny whitefly (Aleurocanthus spiniferus), Acamar scale insects (Aonidiella aurantii), Sanho zero scale insects (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), Ruby Roe beetle (Ceroplastes rubens), Iceria scale insect (Icerya purchasi), Fujino scale insect (Pranococcus kraunhiae), Swan scale scale (Pseudococcus long) ispinis), scale insects such as Pseudouracapis pentagona, bedbugs, bed bugs such as Chime lectularius, and whales.

Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Common moths such as Shibatatsuga (Pediasia teterrellus), Lotus moth (Spodoptera litura), Spodoptera exigua, Ayuyotoga (Pseudaletia separata), Yotoga Mestra brassicae, Agrotis ipsilon, Tamanagine waiba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpas, etc .; (Leguminivora glycinivolora), Azusa yamashiga (Matsumuraeses azukivorora), apple wolfberry (Adoxophyes orana fasciata), chanokokumon hamakihaki (Adohomocha maki). a), Japanese horseshoe moths (Archips fuscocuppreanus), codling moths (Cydia pomonella), etc .; Anopheles, Limantria, Euproctinis, etc., Suga, such as Plutella xylostella, Peptinophora gossypiella, Phthorimaea, Olycelli, H. Hitrigues such as ria cunea, and Hirokosukoga such as iga (Tinea translucens) and koiga (Tineola bisselliella).

Thrips of the order Thrips thrips, Sriptotrips dorsalis, Sriptorips dorsalis

Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc. Moguribae (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, fleas such as Megaselia spiracularis, Clogmial etc. Flies such, blackfly acids, Abu such as gadfly (Tabanus trigonus), and stable flies and the like.

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Maizeweville (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Azuki weevil (Callosobrchuchus chiensis), Rice weevil (Echinocnemus squatius) Weevil (Anthonomus grandis), Weevil weevil (Sphenophorus venatus) and other weevil, Tenebrio molitor, Aureum oleume olium (Olymoidum) Leaf beetles such as Phyllotreta striola, Colorado potato beetle (Leptinotarsa decemlineata), Japanese beetle ant beetle (Anthrenus versaci), Dermatodes sulculates, etc. Shimushi, Shibamushi (Lasiderma serricorne), etc .; Japanese beetles, longicorn beetles such as Anophorora malasiaca, click beetles (Agriotes spp.), And long-horned beetle (Paederus fuscipes).

Pterodoptera: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, Oroja japonica, etc.

Insect pests: cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mouse fleas (Xenopsilla cheopes) and the like.

Lice insect pests: Japanese lice (Pediculus humnus corporis), pheasants (Phythrus pubis), cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ostois aus pis)

Hymenoptera: Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Such as ants, hornets, hornets, bees (Athalia rosae), Japanese bees (Athalia japonica), and the like.

Cockroach eye pests: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta fuliginosa), Cockroach cockroach (Periplaneta americana), Japanese cockroach (Peripraneta bruna)

Termite pests: Yamato termites (Reticulitermes supertus), Japanese termites (Coptothermes formosanus), American white termites (Incitermes minors), Cyptotermes domesticus, Glypoptermes satsumensis, Gyptotermes nakajimai, Caterpillars (Glyptotermes fuscus), Termites (Glypoptermes kodamai), Shimotoshiroari (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis ), Termites termites (Pericapritermes nitobei), termites termites (Sinocapriters mushae), Reticulitermes fl ipes, Reticulitermes hesperus, Reticulitermes virginicus, Reticulitermes tibialis, Heterotermes aureus, Zootermopsis nevadensis or the like.

Mite order pests: Tick spider mites (Tetranychus urticae), Tick spider mites (Tetranychus kanzawai), citrus spider mite (Pananychus citri), mite spider mite (Panthonychus ulmi), prickly mite pistols, citrus urticae Tomato rust mites (Aculops lycopersici), Chanosabi mites (Calacarus carinatus), Chanogasabi mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple scab mites Achulus schizus endali) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), Tick ticks (Ixodes ovatus), Tick ticks (Ixodes persulcatus), Black legged ticks (Ixodes scapularis), Boophilus microplus, Rhipic mite (Rhipic) phalus sanguineus) ticks such as, Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), house dust mite such as pteronyssinus (Dermatophagoides ptrenyssnus), Hosotsumedani (Cheyletus eruditus), Stag Tsumedani ( Tilet mites, such as Cheyletus malaccensis, and Mite thorny (Cheyletus moorei), house dust mite (Ornithonysus bacoti), bird mite (Ornithonysus sylvairum) , Cucumbers such as Dermanysusus gallinae, tsutsugamushi such as Leptotropidum akamushi, and Chiracantium japonicum etc.

Lip limb class: Geji (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes), etc.

Double-legged class: Oxidus gracilis, Nadeyopus tambanus, etc.

Isopods: Armadillium vulgare, etc.

Gastropods: Limax marginatus, Limax flavus, etc.

Nematodes: rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematode (Globodera rostochiensis), southern nematode nectar (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus) and the like.

The pest control agent of the present invention contains the compound of the present invention and an inert carrier. The pest control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, etc., and if necessary, a surfactant and other formulation adjuvants are added. Thus, they are formulated into emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smoke agents, poison baits, resin formulations and the like.

The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.

Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine fertilizers such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.) and granular materials.

Examples of liquid carriers include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons. (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyrate) Nitriles), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).

Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and the like, and alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. An ionic surfactant is mentioned.

Examples of other formulation adjuvants include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention directly to pests and / or to habitats of pests (plants, soil, households, animal bodies, etc.). . In the pest control method of the present invention, the compound of the present invention is usually used in the form of the pest control agent of the present invention.

When the pest control agent of the present invention is used for pest control in the agricultural field, the application amount is 1 to 10,000 g in the amount of the present compound per 10,000 m ² . When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10,000 ppm. Agents, powders, etc. are usually applied as they are.

These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit the soil of cultivated land. You may process to soil.

Also, it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.

When the pest control agent of the present invention is used for controlling pests living in a house, the amount applied is the amount of the compound of the present invention per 1 m ² of treatment area when treated on the surface, usually 0.01. In the case of treatment in a space, the amount of the compound of the present invention per 1 m ³ of the treatment space is usually 0.01 to 500 mg. When the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 1000 ppm. Apply aerosols, smoke, poisonous bait, etc. as they are.

The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.

Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.

Fruit trees: apples, pears, Japanese pears, quince, quince, etc., nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (citrus mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.

Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, eel, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.

Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, blue whale, etc.

Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), biofuel plants (Jatropha, Curcas, safflower, Amanasuna, switchgrass, Miscanthus, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.), ornamental plants, etc. .

“Crop” includes genetically modified crops.

The pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are shown below.

Active Ingredients of Insecticide (1) Carbamate Compounds Alaniccarb, Aldicarb, Bendiocarb, Benfurcarb, Butocaboxim, Butoxycarbyl, Butoxycarboxyl = NAC), Carbofuran, Carbosulfan, Cloethocarb, Ethiofencarb, Fenobucarb (BPMC), Fenothiocarb (Fenothiocarb, Fenothiocarb) ratiocarb, isoprocarb (Isoprocarb = MIPC), methiocarb (Methiocarb), methomyl (Methomyl), metorcarb (Metocarb), oxamyl (Oxamyl), pirimicarb (Pro), propoxyl (Pro) ), Triazamate, Trimesacarb, XMC, and Xylylcarb.

(2) Organophosphorus compounds: Acetate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Kazusafos, Chlorethhosphine, Chlorethophos , Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos = CYAP, Demeton-S-methyl, Demethon-S Jiku Rubos (Dichlorvos = DDVP), Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Etoprofos, Ethoprophos ), Fenamiphos, Fennitrothion (MEP), Fenthion (MPP), Phosphiazate, Heptenophos (Imicyfos), Ifenfos (Ipofos) Ethoxyaminothio-phosphoryl) salicylate, isoxathion (Isoxathion), malathion (Malathion), mecarbam (Mecarbom), mesulfophos (Mesulfofos), methobin (Methodophos), methidophos (Methidophos) (Naled: BRP), Omethoate, Oxydemethon-methyl, Parathion, Methylparathion, Phenthoate = PAP Phorate, Phosalone, Phosmet = PMP, Phosphamidon, Phoxim, Pirimiphos-methi, Profenfos (Pro), Profenfos (Pro), Profenfos (Profenfos) , Pyrachlorfos, pyridafenthion, quinalphos, sulfotep, tebupyrimfos, temephos, terubfos, terbufos, terbufos, terbufos nphos), thiomethon (Thiomethon), triazophos (Triazophos), trichlorphone (TRICHLPHON = DEP), bamidthione (Vamidothion), aluminum phosphide (Phiothiophene), rothiophos Formothion, Hydrogen phosphide, Oxydeprofos (ESP), Propafos, Salithion, and Sulprofos.

(3) Pyrethroid compounds Acrinathrin, Allethrin, Benfluthrin, Beta-Cyfluthrin, Bifenthrin, Cycloprothrin, Cycloprothrin (Cycloprothrin, Cycloprothrin, Cycloprothrin) , Cypermethrin, Deltamethrin, Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Fulcitrate F lucytrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praletrin, prethrin. Resmethrin, Sigma-Cypermethrin, Silafluofen, Tefluthrin, Tralomethrin, Transfluthrin, Tetramethrin thrin), phenothrin, cyphenothrin, alpha-Cypermethrin, zeta-Cypermethrin, lambda cihalothrin (lambda-Cyhalothrin) ), Furamethrin, tau-fluvalinate, methofluthrin, profluthrin, dimethylfluthrin, trifluorophenbute5, protrifenbute5, protrifenbute5 4- (Methoxyme L) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4-
(Methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate and the like.

(4) Nereistoxin compounds Cartap, Bensulpap, Thiocylam, Thiosultap, Monosultap, and Bisultap.

(5) Neonicotinoid compounds Imidacloprid (Imidac1oprid), Nitenpyram (Nitenpyram), Acetamiprid (Acetamiprid), Thiamethoxam (Thiamethoxam), Thiacloprid (An) and dinotefurin (in)

(6) Benzoylurea compounds Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexafluuron, Hexafluuron Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron, and fluazuuron.

(7) Phenylpyrazole compounds Acetoprole, Ethiprole, Fipronil, Vaniliprole, Pyriprole, and Pyrafluprole.

(8) Bt toxin insecticide Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.

(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.

(10) Organochlorine compounds Aldrin, Dieldrin, Dienochlor, Endosulfan, Methoxychlor, Chlordane, and DDT.

(11) Other Insecticide Active Ingredients Machine oil (Machine oil), nicotine sulfate (Nicotine-sulfate), nicotine (Nicotine), abamectin (Abamectin), emamectin benzoate (Emamectin-benzoate), milbemectin (Milbemectin) (Lepidectin), Spinosad, Spinetoram, Indoxacarb, Metaflumizone, Buprofezine, Cyromene, Cyromene, Cyromene, Cyromene ), Pyriproxyfen, Phenoxycarb, Chlorphenapyr, DNOC, Diafenthiuron, Pymetrozine, Pymetrozine, Pymetrozine Tolfenpyrad, Flurimfen, Flufenerim, Spirotetramat, Spiromesifen, Sulfoxaflor, Chloranthrolitrol orantraniliprole, cyantraniliprole, fulvendiamide,
The following formula (K):

[Where,
R ¹⁰⁰ represents a chlorine atom, a bromine atom or a trifluoromethyl group,
R ²⁰⁰ represents a chlorine atom, a bromine atom or a methyl group,
R ³⁰⁰ represents a chlorine atom, a bromine atom or a cyano group. ]
A compound represented by
The following formula (L):

[Where,
R ¹⁰⁰⁰ represents a chlorine atom, a bromine atom or an iodine atom. ]
, Methoxadiazone, sulfuramide, arsenous acid, benclothiaz, lime nitrogen (Calcium flude) (Calcium flude) ammonium, Metam-sodium, Potassium oleate, Sulfur, and Tralopyril.

Active ingredients of acaricides: Acequinocyl, Amitraz, Benzoximate, Bifenaate, Bromopropyl, BSPC, Chromethionate, Chromethionate ), Clofentezine, cyflumetofen, dicofol, etoxazole, fenazaquin, fenbutatin oxide, fenothiophen Pyroximate, Fluacrylpyrim, Hexythiaxox, propargite (di), di (R), pyridene (P), piridaben (Pyriben) Diclofen, Spirodiclofen, Amidoflumet, and Cyenopyrafen.

Active ingredient of nematicide Methyl bromide, DD (1,3-Dichloropropene), DCIP, Fostiazate, levamisole hydrochloride, Levimisol, Methylisothiocyanate tartarate), and Imicyafos.

Active ingredients of fungicides Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Difenaconol, Dinicoconol D, Iniconazole E (Fenarimol) Fenbuconazole, Flucilazole, Fluquinconazole, Flutriafol, Hexaconazole, Imazaril (Imazalil) Imibenconazole, Ipconazole, Iconconazole, Metconazole, Microbutanil, Nuarimol, Oxpoconazole, Puroazo Propiconazole, Prothioconazole, Pyrifenox, Simeconazole, Tebuconazole, Tetraconazole, Triazimone fon), triadimenol (Triadimenol), triflumizole (Triflumizole), trifolin (Trifolin), triticonazole (Triticonazole), aldimorph (Dodimorph), dodemorph (Morph) , Fenpropidin, Piperalin, Spiroxamine, Fenhexamide, Pyributicarb, Naftifine, Terbinafine (Terbinafine)
Benomyl, Carbendazim, Fuberidazole, Thiabendazole, Thiophaneate, Thiophaneate, ThiophanateMethyl, ThiophanateMethyl ) And other cell division inhibiting bactericidal compounds;
Clozolinate (Chlozolinate), Iprodione (Iprodione), Procymidone (Procymidone), Vinclozoline (Quinoxyfen), Proquinazin (Proquinodil), Fenpiclonil (Fenpiclonil)
Bactericidal compounds that inhibit amino acid biosynthesis such as cyprodinil, pyrimethanil, mepanipyrim;
Bactericidal compounds that inhibit nucleic acid biosynthesis, such as metalaxyl, benalaxyl, oxolinic acid;
Isoprothiolane (Iproprotiolane), Iprobenfos (Iprobenfos), Toluclofos-methyl (Prothiocarb), Dimethomorphic (Benthiatropiprob) Bactericidal compounds that inhibit lipid and membrane synthesis;
Melanin biosynthesis inhibiting bactericidal compounds such as diclocymet, carpropamide, phenoxanil, fthalide, tricyclazole, pyroquilon, etc .;
Azoxystrobin, dimoxystrobin, enestrobin, fluoxastrobin, cresoxime-methyl, methinostrobin (methominostrobin) Strobilurin bactericidal compounds such as Pyroxystrobin, Pyraclostrobin, Pyribencarb Trifloxystrobin;
Carboxin, Oxycarboxin, Mepronil, Flutolanil, Furametopyr, Thifluzamide, Flupy, penthirid, P Anilide bactericidal compounds such as Bixafen, Isopyrazam, Penflufen, Sedaxan, Fluxapyroxad;
Resistance-inducing compounds such as Acibenzolar-S-methyl, Probenazole, Tiadinil, Isotianil;
Glucan synthesis-inhibiting fungicidal compounds such as validamycin A and polyoxin B;
Protein biosynthesis inhibiting bactericidal compounds such as Blastcidin-S, Kasugamycin, Streptomycin, etc .;
Thiuram, Mancozeb, Chlorothalonil, Captan, Diclofluanid, Folpet, Iminoctaine, Bacteria of Ziram (Zira) Compound; Amisulbrom; Cyazofamid; Ferimzone; Fluazinam; Binapacryl; Dinocapone; Famoxadone; Famoxadon; etrafenone); cyflufenamid (Cyflufenamid) and the like.

Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (Phenothio1), mecoprop (Fluoxypyr), triclopyr (Triclopyr), Clomeprop, Clomeprop Naproanilide.

(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.

(3) Urea herbicidal compounds diuron (Diuron), linuron (Linuron), chlortoluron (Chlortururon), isoproturon (Isoproturon), fluometuron (Isouron) (Isouron), Tebutiuron (Tebuthuron (Tebuthuron) , Cumyluron, Daimuron, and Methyl-daimuron.

(4) Triazine herbicidal compounds Atrazine, Ametrine, Cyanazine, Simazine, Propazine, Simetrin, Dimetamethrin, Dimethamethrin ), Triaziflam, and indaziflam.

(5) Bipyridinium herbicidal compound Paraquat and Diquat.

(6) Hydroxybenzonitrile herbicidal compound Bromoxynil and Ioxynil.

(7) Dinitroaniline herbicidal compound Pendimethalin, Prodiamine, and Trifluralin.

(8) Organophosphorus herbicidal compounds Amiprofos-methyl, Butamifos, Bensulide, Piperophos, Anilofos, Glyphosate, Glufonate, Glufonate P (Glufosinate-P), and Bialaphos.

(9) Carbamate herbicidal compound: Di-allate, Tri-alate, EPTC, Butyrate, Benchiocarb, Esprocarb, Molinate, Dimepiperate, Dimepiperate (Swep), Chlorprofham, Phenmedifam, Phenisopham, Pyributicalb, and Asuram.

(10) Acid amide herbicidal compound Propanil, Propyzamide, Bromobutide, and Etobenzanide.

(11) Chloroacetanilide herbicidal compounds Acetochlor, Alaclor, Butachlor, Dimethenamide, Propaclor, Metazachlor, Metolachlor, Metolachlor Pretilachor), tenylchlor (Theny1ch1or), and petoxamide (Pethoxamide).

(12) Diphenyl ether herbicidal compound acifluorfen (Acifluorfen-sodium), bifenox (Oxyfluorfen), lactofen (Lactofen), fomesafen (Chlophenoxy), clomethoxypheny (Chlophenoxy)

(13) Cyclic imide herbicidal compounds Oxadiazone, Cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumilacrac-pentyl Oxazine (Flumioxazin), Pyraflufen-ethyl, Oxadiargyl (Oxadialy), Pentoxazone, Fluthiacet-methyl, Butafenzene (Butafenzil) azone), and saflufenacil.

(14) Pyrazole herbicidal compounds: Benzofenap, Pyrazolate, Pyrazoxifene, Topramzone, and Pyrasulfotole.

(15) Triketone herbicidal compounds Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefril trione.

(16) Aryloxyphenoxypropionic acid herbicidal compound Clodinafop-propargyl, Cyhalofop-butyl, Diclohop-methyl, Fenoxaprop-ethyl Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, and metamihop.

(17) Trione oxime herbicidal compounds Alloxydim-sodium, cetoxydim, Butroxidim, Crethodim, Cloproxidim, Cyclodimoxime (Tralkoxydim), and Profoxydim.

(18) Sulphonylurea herbicidal compound Chlorsulfuron, Sulfomethuron-methyl, Metsulfuron-methyl, Chlorimuron-ethyl, Tribenuron methyl Tribenuron-methyl), trisulfuron (Triasulfuron), bensulfuron-methyl (Bensulfuron-methy1), thifensulfuron-methyl (Pyrazsulfuron-methyl), pyrysulfururon-methyl- (1) Nicosulfuron (Nico sulfuron, amidosulfuron, minosulfuron, imosulfuron, rimsulfuron, halosulfuronmethyl (Halsulfuron-sulfuron) , Triflusulfuron-methyl, frazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azulfurium Azulsulfuron, ethoxysulfuron, oxasulfuron, sodium iodosulfuron methyl sodium (Idosulfuron-methyl-sodium), foramsulfuron, mesosulfuron methyl Trisulfursulfuron, Tritosulfuron, Orthosulfururon, Flucetosulfuron, and Propyrisulfuron.

(19) Imidazolinone herbicidal compounds Imazametabenzmethyl (Imazamethapyr), imazamoxyl, imazapyr (i), imazapir (in), imazakin (in)

(20) Sulfonamide herbicidal compounds Flumeslam, Methoslam, Diclosram, Floraslam, chloranthramx, Penoxsulox and Penoxsulox.

(21) Pyrimidinyloxybenzoic acid herbicidal compound Pyrithiobac-sodium, Bispyribac-sodium, Pyriminobac-methyl1, Pyribenzoximf, Pyribenzoximf And Pyrimisulfan.

(22) Other herbicidal compounds: Bentazone, Bromasil, Terbacil, Chlorthiamid, Isoxaben, Dinoseb, Amitrol, Methiline, C Tridiphane, Dalapon (Dalapon), Diflufenzopyr sodium (Diflufenzopyr-sodium), Dithiopyr (Dhithiopyr), Thiazopyr (Thiazopyr), Sodium Flucarbazone (Prolucazone) Mefenacet, Flufenacet, Fentrazamide, Cavenstrole, Indanofan, Oxiclomelate, Benfrecetate, Benfrateto (Norflurazon), flulutamon (Diflufenican), diflufenican, picolinafene (Picolinafene), beflubutamide (Clozoneone), amicarbazone (Amicarzone) , Pinoxaden (Pinoxaden), pyraclonil (Pyraclonil), pyroxasulfone (Pyroxasulfone), thien-carbazone methyl (Thiencarbazone-methyl), amino cyclo Pila crawl (Aminocyclopyrachlor), type phen carbazone (Ipfencarbazone), and Mechiozorin (Methiozolin).

Active ingredient of synergist Piperonyl butoxide, Sesamex, Sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-di Carboximide (MGK 264), N-decrimimidazole (N-Declinimidazole), WARF-anti-resistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenyl butyl Tenon (t-Phenylbutenone), Diethylmaleate, DMC, FDMC, ETP, and ETN.

Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.

First, production examples of the compound of the present invention are shown below.

Production Example 1
Preparation of 4- (5-Neopentylthiophen-2-yl) -pyridine (Compound 1-18)

(1) 2.08 g of 1- (5-bromothiophen-2-yl) -2,2-dimethylpropan-1-ol, 1.13 g of 4-pyridineboronic acid, [1,1′-bis (diphenylphosphino) ) A mixture of 0.34 g of ferrocene] dichloropalladium methylene chloride complex, 8.85 g of tripotassium phosphate n-hydrate and 16 mL of 1,4-dioxane was refluxed for 3 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered through celite. The aqueous layer was extracted with ethyl acetate, and then the organic layer was washed with water and dried over anhydrous magnesium sulfate. After concentrating the solvent under reduced pressure, the obtained residue was subjected to silica gel chromatography, and 2,2-dimethyl-1- (5-pyridin-4-yl-thiophen-2-yl) -propan-1-ol 0 .61 g was obtained.
¹ H-NMR (CDCl ₃ ) δ: 1.02 (9H, s), 2.29 (1H, br s), 4.66 (1H, d), 6.95 (1H, d), 7.38 (1H, d), 7.45 (2H, dd), 8.56 (2H, dd).

(2) 2,2-dimethyl-1- (5-pyridin-4-yl-thiophen-2-yl) -propan-1-ol 0.61 g, 1,1′-thiocarbonyldiimidazole 0.87 g, 4 A mixture of 30 mg of dimethylaminopyridine and 18 ml of toluene was refluxed for 8 hours. Ethyl acetate and methanol were added to the cooled reaction mixture, washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentrating the solvent under reduced pressure, the resulting residue was subjected to silica gel chromatography,

0.55 g of the compound (M1) represented by
¹ H-NMR (CDCl ₃ ) δ: 1.19 (9H, s), 4.97 (1H, s), 7.07-7.09 (2H, m), 7.34 (1H, d), 7.42-7.46 (3H, m), 8.18 (1H, s), 8.58 (2H, dd).

(3) A mixture of 0.55 g of compound (M1), 0.62 ml of tributyltin hydride, 38 mg of 2,2′-azobis (2-methylpropionitrile) and 30 ml of toluene was refluxed for 2 hours. 1N hydrochloric acid was added to the reaction mixture which had been allowed to cool, and the phases were separated. The aqueous layer was washed with toluene, neutralized with an aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer extracted with ethyl acetate was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.21 g of 4- (5-neopentylthiophen-2-yl) -pyridine.

Production Example 2
Preparation of 4- (5-Neopentylfuran-2-yl) -pyridine (Compound 2-18)

(1) To a mixture of 2.50 g of 2,5-dibromofuran and 100 ml of tetrahydrofuran, 7.8 ml of n-butyllithium (1.6M hexane solution) was added dropwise at −78 ° C., and then at −78 ° C. for 1 hour. Stir. Next, 1.80 ml of trimethylacetaldehyde was added dropwise at -70 ° C. The temperature was raised to −10 ° C., and a saturated aqueous ammonium chloride solution was poured into the reaction solution. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 1.83 g of 1- (5-bromofuran-2-yl) -2,2-dimethylpropan-1-ol.
¹ H-NMR (CDCl ₃ ) δ: 0.97 (9H, s), 4.32 (1H, d), 6.21 (1H, d), 6.25 (1H, d).

(2) 1.83 g of 1- (5-bromofuran-2-yl) -2,2-dimethylpropan-1-ol, 1.06 g of 4-pyridineboronic acid, [1,1′-bis (diphenylphosphino) A mixture of ferrocene] dichloropalladium methylene chloride complex 0.32 g, tripotassium phosphate n-hydrate 8.33 g and 1,4-dioxane 13 mL was refluxed for 4 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered through celite. The aqueous layer was extracted with ethyl acetate, and then the organic layer was washed with water and dried over anhydrous magnesium sulfate. After concentrating the solvent under reduced pressure, the obtained residue was subjected to silica gel chromatography, and 2,2-dimethyl-1- (5-pyridin-4-yl-furan-2-yl) -propan-1-ol 0 .98 g was obtained.
¹ H-NMR (CDCl ₃ ) δ: 1.02 (9H, s), 2.08 (1H, br s), 4.45 (1H, d), 6.38 (1H, d), 6.84 (1H, d), 7.47 (2H, dd), 8.58 (2H, dd).

(3) 2,2-dimethyl-1- (5-pyridin-4-yl-furan-2-yl) -propan-1-ol 0.98 g, 1,1′-thiocarbonyldiimidazole 0.58 g, 4 -A mixture of 26 mg of dimethylaminopyridine and 20 ml of toluene was refluxed for 2 hours. Ethyl acetate and methanol were added to the cooled reaction mixture, washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentrating the solvent under reduced pressure, the resulting residue was subjected to silica gel chromatography,

0.71 g of the compound (M2) represented by
¹ H-NMR (CDCl ₃ ) δ: 1.09 (9H, s), 6.15 (1H, d), 6.29 (1H, d), 6.78-6.81 (2H, m), 7.18 (1H, d), 7.46-7.49 (3H, m), 8.58 (2H, dd).

(4) A mixture of 0.71 g of compound (M2), 0.83 ml of tributyltin hydride, 51 mg of 2,2′-azobis (2-methylpropionitrile) and 20 ml of toluene was refluxed for 4 hours. 1N hydrochloric acid was added to the reaction mixture which had been allowed to cool, and the phases were separated. The aqueous layer was washed with toluene, neutralized with an aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer extracted with ethyl acetate was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.12 g of 4- (5-neopentylfuran-2-yl) -pyridine.

Production Example 3
Preparation of 4- (1-Neopentylpyrrol-3-yl) -pyridine (Compound 3-18)

A mixture of 0.15 g of 4- (pyrrol-3-yl) -pyridine, 0.31 g of neopentyl iodide, 50 mg of sodium hydride (60% mineral oil mixture) and 2 ml of N, N-dimethylformamide at 90 ° C. for 2 hours Stir. A saturated aqueous ammonium chloride solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.18 g of 4- (1-neopentylpyrrol-3-yl) -pyridine.

Production Example 4
Preparation of 4- (1-Neopentylpyrazol-3-yl) -pyridine (Compound 4-18)

A mixture of 0.20 g of 4- (pyrazol-3-yl) -pyridine, 0.33 g of neopentyl iodide, 66 mg of sodium hydride (60% mineral oil mixture) and 3 ml of N, N-dimethylformamide at 100 ° C. for 2 hours Stir. A saturated aqueous ammonium chloride solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.26 g of 4- (1-neopentylpyrazol-3-yl) -pyridine.

Production Example 5
Production of 4- (1-neopentylpyrazol-3-yl) -3-fluoropyridine (Compound 4-19)

(1) A mixture of 0.44 g of 4-acetyl-3-fluoropyridine and 5 ml of N, N-dimethylformamide dimethylacetal was refluxed for 2 hours. The solvent was concentrated under reduced pressure to obtain 0.61 g of 3-dimethylamino-1- (3-fluoropyridin-4-yl) -2-propen-1-one.
¹ H-NMR (CDCl ₃ ) δ: 2.94 (3H, s), 3.19 (3H, s), 5.59 (1H, d), 7.64 (1H, br s), 7.89 (1H, br s), 8.47 (1H , dd), 8.51 (1H, d).

(2) A mixture of 0.61 g of 3-dimethylamino-1- (3-fluoropyridin-4-yl) -2-propen-1-one, 0.15 ml of hydrazine (hydrate) and 19 ml of ethanol at 80 ° C. Stir for hours. After the solvent was concentrated under reduced pressure, the obtained residue was subjected to silica gel chromatography to obtain 0.45 g of 3-fluoro-4- (pyrazol-3-yl) -pyridine.
¹ H-NMR (CDCl ₃ ) δ: 6.90 (1H, t), 7.71 (1H, d), 7.88 (1H, t), 8.46 (1H, dd), 8.56 (1H, d).

(3) 0.45 g of 3-fluoro-4- (pyrazol-3-yl) -pyridine, 0.66 g of neopentyl iodide, 0.17 g of sodium hydride (60% mineral oil mixture) and N, N-dimethylformamide 3 ml of the mixture was stirred at 100 ° C. for 8 hours. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.42 g of 4- (1-neopentylpyrazol-3-yl) -3-fluoropyridine.

Production Example 6
Production of 4- (1-Neopentylpyrazol-3-yl) -3-methoxypyridine (Compound 4-24)

A mixture of 0.21 g of 4- (1-neopentylpyrazol-3-yl) -3-fluoropyridine, 1.70 g of sodium methoxide (28% methanol solution) and 2.5 ml of N, N-dimethylformamide at 100 ° C. For 1 hour. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.19 g of 4- (1-neopentylpyrazol-3-yl) -3-methoxypyridine.

Production Example 7
Preparation of 4- (1-Neopentylpyrazol-3-yl) -3- (methylthio) pyridine (Compound 4-27)

A mixture of 0.21 g of 4- (1-neopentylpyrazol-3-yl) -3-fluoropyridine, 0.13 g of sodium thiomethoxide and 2.0 ml of N, N-dimethylformamide was stirred at room temperature for 5 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.23 g of 4- (1-neopentylpyrazol-3-yl) -3- (methylthio) pyridine.

Production Example 8
Preparation of 4- (4-methyl-1-neopentylpyrazol-3-yl) -pyridine (Compound 4-40)

A mixture of 0.20 g of 4- (4-methylpyrazol-3-yl) -pyridine, 0.37 g of neopentyl iodide, 60 mg of sodium hydride (60% mineral oil mixture) and 2 ml of N, N-dimethylformamide at 110 ° C. For 4 hours. A saturated aqueous ammonium chloride solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.26 g of 4- (4-methyl-1-neopentylpyrazol-3-yl) -pyridine.

Production Example 9
Preparation of 4- (5-methyl-1-neopentylpyrazol-3-yl) -pyridine (Compound 4-46)

A mixture of 0.20 g of 4- (5-methylpyrazol-3-yl) -pyridine, 0.37 g of neopentyl iodide, 60 mg of sodium hydride (60% mineral oil mixture) and 2 ml of N, N-dimethylformamide at 100 ° C. For 4 hours. A saturated aqueous ammonium chloride solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.26 g of 4- (5-methyl-1-neopentylpyrazol-3-yl) -pyridine.

Production Example 10
Preparation of 4- (1-Neopentylpyrazol-3-yl) -pyrimidine (Compound 4-51)

A mixture of 0.17 g of 4- (pyrazol-3-yl) -pyrimidine, 0.45 g of neopentyl iodide, 68 mg of sodium hydride (60% mineral oil mixture) and 3 ml of N, N-dimethylformamide at 100 ° C. for 8 hours Stir. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.14 g of 4- (1-neopentylpyrazol-3-yl) -pyrimidine.

Production Example 11
Preparation of 4- (1-Neopentylpyrazol-4-yl) -pyridine (Compound 4-84)

A mixture of 0.18 g of 4- (pyrazol-4-yl) -pyridine, 0.37 g of neopentyl iodide, 59 mg of sodium hydride (60% mineral oil mixture) and 2 ml of N, N-dimethylformamide at 100 ° C. for 4 hours. Stir. A saturated aqueous ammonium chloride solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.26 g of 4- (1-neopentylpyrazol-4-yl) -pyridine.

Production Example 12
Preparation of 4- (1-Neopentyl- [1,2,4] triazol-3-yl) -pyridine (Compound 5-18)

0.25 g of 4-([1,2,4] triazol-3-yl) -pyridine, 0.51 g of neopentyl iodide, 82 mg of sodium hydride (60% mineral oil mixture) and N, N-dimethylformamide 5 ml of the mixture was stirred at 100 ° C. for 2 hours. A saturated aqueous ammonium chloride solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.15 g of 4- (1-neopentyl- [1,2,4] triazol-3-yl) -pyridine）.

Production Example 13
Preparation of 4- (3-Neopentylpyrazol-1-yl) -pyridine (Compound 6-18)

A mixture of 0.30 g of 3-neopentylpyrazole, 1.64 g of 4-chloropyridine hydrochloride, 1.51 g of potassium carbonate and 6 ml of N-methylpyrrolidinone was stirred at 100 ° C. for 4 hours. Saturated sodium hydrogen carbonate solution was poured into the reaction mixture which had been allowed to cool, and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.23 g of 4- (3-neopentylpyrazol-1-yl) -pyridine.

Production Example 14
Preparation of 4- (3-Neopentyl- [1,2,4] triazol-1-yl) -pyridine (Compound 7-18)

A mixture of 0.35 g of 3-neopentyl- [1,2,4] triazole, 1.62 g of 4-chloropyridine hydrochloride, 1.50 g of potassium carbonate and 6 ml of N-methylpyrrolidinone was stirred at 110 ° C. for 4 hours. Saturated sodium hydrogen carbonate solution was poured into the reaction mixture which had been allowed to cool, and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.33 g of 4- (3-neopentyl- [1,2,4] triazol-1-yl) -pyridine.

Hereinafter, the compounds produced by the production method according to the method described in the above-mentioned Example Production Example will be exemplified.

In the table, Me is a methyl group (CH ₃ —), Et is an ethyl group (CH ₃ CH ₂ —), Pr is a propyl group (CH ₃ CH ₂ CH ₂ —), and i-Pr is an isopropyl group ((CH ₃ )). ₂ CH—) and t-Bu represent a tert-butyl group ((CH ₃ ) ₃ C—), and sec-Bu represents a sec-butyl group (CH ₃ CH ₂ CH (CH ₃ ) —).

In the table, in the column “(E ¹ ) _n ”, when n is 1, for example, “3-Me” is indicated, which is the 3-position of the heteroaromatic ring in which E ¹ is represented by Het. It means that it is a substituted methyl group, and when n is 0, it is shown as “-”, which means that it is unsubstituted.

Compound represented by formula (A-1).

In the formula, the JLA group, (E ¹ ) _n , D, G and m represent the combinations described in the following [Table 2] to [Table 3]. Hereinafter, Q represents the following formula.

Compound represented by formula (A-2).

In the formula, the JLA group, (E ¹ ) _n , D, G and m represent the combinations described in the following [Table 4] to [Table 5].

Compound represented by formula (A-3).

The JL group, (E ¹ ) _p , D, G and m in the formula represent the combinations described in the following [Table 6] to [Table 7].

Compound represented by formula (A-4).

The JL group, (E ¹ ) _n , D, G and m in the formula represent the combinations described in the following [Table 8] to [Table 12].

Compound represented by formula (A-5).

The JL group, E ¹ , D, G and m in the formula represent the combinations described in the following [Table 13] to [Table 14].

Compound represented by formula (A-6).

In the formula, the JLA group, (E ¹ ) _n , D, G and m represent the combinations described in the following [Table 15] to [Table 18].

A compound represented by formula (A-7).

In the formula, JLA group, E ¹ , D, G and m represent the combinations described in the following [Table 19] to [Table 20].

The physical properties of the compounds of the present invention described in [Table 2] to [Table 20] are shown in the following [Table 21] to [Table 22].

Next, formulation examples of the compound of the present invention are shown. In addition, a part represents a weight part.

Formulation Example 1
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 10 parts of any one of 1 to 6-102 and compounds 7-1 to 7-34 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and 14 parts of polyoxyethylene styrylphenyl ether And 6 parts of calcium dodecylbenzenesulfonate are added and mixed to obtain each emulsion.

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide-containing fine powder and 54 parts of diatomaceous earth were mixed, and the above-mentioned compounds 1-1 to 1-51, compounds 2-1 to 2-34, Any one of Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6-1 to 6-102, and Compounds 7-1 to 7-34 20 Add parts and mix to obtain each wettable powder.

Formulation Example 3
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- Add 1 part of synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay to 2 parts of any one of 1 to 6-102 and compounds 7-1 to 7-34 To do. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.

Formulation Example 4
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- One part of any one of 1 to 6-102 and compounds 7-1 to 7-34 is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide-containing fine powder, 0.3 part of PAP and 93.7 of Fusami clay 93.7 are mixed. Add parts, mix well, and evaporate and remove acetone to obtain each powder.

Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), the above-mentioned compounds 1-1 to 1-51, compounds 2-1 to 2-34, compounds 3-1 to 3 -38, compounds 4-1 to 4-104, compounds 5-1 to 5-38, compounds 6-1 to 6-102, and compounds 7-1 to 7-34 10 parts and water 55 parts Are mixed and finely pulverized by a wet pulverization method to obtain each preparation.

Formulation Example 6
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 0.1 part of any one of 1 to 6-102 and compounds 7-1 to 7-34 is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of deodorized kerosene to obtain each oil agent. Get.

Formulation Example 7
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 10 mg of any one of 1 to 6-102 and compounds 7-1 to 7-34 is dissolved in 0.5 ml of acetone, and this solution is mixed with animal solid feed powder (bred breeding solid feed powder CE-2, Japan Treat to 5g, and mix evenly. Then, acetone is evaporated to dryness to obtain each poisonous bait.

Formulation Example 8
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 0.1 part of any one of 1 to 6-102 and compounds 7-1 to 7-34 and 49.9 parts of neothiozole (Chuo Kasei Co., Ltd.) were placed in an aerosol can and fitted with an aerosol valve. The oil agent aerosol is obtained by filling the part and 25 parts of LPG, adding shaking, and mounting the actuator.

Formulation Example 9
Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 0.6 part of any one of 1 to 6-102 and compounds 7-1 to 7-34, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, Deodorized kerosene 3.39 parts and emulsifier {Atmos 300 (registered trademark name of Atmos Chemical Co., Ltd.)} 1 part mixed and dissolved, and distilled water 50 parts are filled in an aerosol container, and after attaching the valve, Aqueous aerosol is obtained by pressure filling 40 parts of propellant (LPG).

Next, the pest control effect of the compound of the present invention is shown by test examples.

Test example 1
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.

10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the brown planthopper were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthoppers infested with rice was investigated, and the control value was determined by the following formula.

Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.

Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compounds of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.
Compounds 1-18, 2-18, 3-18, 3-35, 4-18, 4-19, 4-24, 4-25, 4-27, 4-30, 4-36, 4-38, 4 -40, 4-42, 4-46, 4-48, 4-51, 4-84, 4-101, 4-102, 4-103, 5-18, 5-36, 6-18, 7-18 .

Test example 2
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test spray solution.

On the other hand, about 30 cotton aphids were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups and left for 1 day. Each of these seedlings was sprayed with 20 ml of the diluted solution.

6 days after spraying, the number of live cotton aphids that parasitized on the cucumber leaves was investigated, and the control value was determined by the following formula.

Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.

Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compounds of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.
Compounds 1-18, 2-18, 3-18, 4-18, 4-19, 4-24, 4-25, 4-27, 4-30, 4-36, 4-40, 4-46, 4 -48, 4-51, 4-84, 4-101, 4-102, 5-18, 5-36, 6-18, 7-18.

The compound of the present invention is useful for controlling pests.

Claims (16)

Formula (1)

[Where,
Het is represented by the following formula H1, H2, H3, H4 or H5:

{Where,
Y ¹ represents —O—, —S— or —NE ² —, Y ² and Y ³ are the same or different and represent —CE ¹ ═ or —N═, and at least one of Y ² and Y ³ Are —CE ¹ ═, Z ¹ , Z ² and Z ³ are the same or different and represent —CE ¹ ═ or —N═ (where E ¹ has one or more halogen atoms) Represents a C1-C2 alkyl group, a hydrogen atom or a halogen atom, and E ² represents a C1-C2 alkyl group which may have one or more halogen atoms.) The mark represents the position where A is combined. } Represents a 5-membered heterocycle represented by
J is the following formula J1 or J2:

(Where
R ¹ and R ² are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
R ⁴ and R ⁵ are the same or different and each represents a methyl group or an ethyl group;
R ⁶ represents a hydrogen atom or a C1-C6 chain hydrocarbon group. ) Represents a group represented by
L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms,
A represents a single bond, —O—, or —S (O) _x — when Het is a group represented by the formula H1, H2, H3 or H5 (where x represents 0, 1 or 2). And represents a single bond when Het is a group represented by formula H4,
G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or the following formulas G1, G2, G3 or G4:

(Where
R ^a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T ¹ which may have one or more atoms or groups selected from <Group α>;
R ^b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, —C (O) —T ² , —S (O) ₂ —. T ^{3 represents} a C3-C9 trialkylsilyl group or a cyclopropyl group,
R ^c represents a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, —C (O) —T ² or a cyclopropyl group;
z represents 0, 1 or 2;
R ^d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group β>, —C (O) —T ² , —S (O) ₂ —. Represents T ³ or a cyclopropyl group,
R ^e represents a C1-C6 chain hydrocarbon group, hydrogen atom or cyclopropyl group which may have one or more atoms or groups selected from <Group β>;
T ¹ has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, a hydroxyl group, an amino group, a hydrogen atom or a cyclopropyl group,
T ² has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, an amino group, a hydrogen atom or a cyclopropyl group,
T ³ represents a C1-C6 alkyl group which may have one or more halogen atoms. ) Represents a group represented by
D represents —N═ or —CH═,
m represents 0 or 1;
<Group α>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms A group consisting of an amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, a C3-C9 trialkylsilyl group, and a cyclopropyl group;
<Group β>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms An amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a phenyl group (the phenyl group is one selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group) And a group consisting of a halogen atom, a cyano group, a C3-C9 trialkylsilyl group, and a cyclopropyl group.
However, the compounds corresponding to the following (1) to (6) are excluded:
(1) Het is a group represented by the formula H1, Y ¹ is —S—, Y ² and Y ³ are —CH═, A is —O—, L is a single bond, A compound in which J is a group represented by formula J1, R ¹ , R ² and R ³ are all methyl groups, G is a hydrogen atom, D is —CH═ and m is 0 ,
(2) Het is a group represented by the formula H1, Y ¹ is —O—, Y ² and Y ³ are —CH═, A and L are single bonds, and J is represented by the formula J2. A compound in which R ⁴ , R ⁵ and R ⁶ are all methyl groups, G is a hydrogen atom, D is —CH═, and m is 0,
(3) Het is a group represented by the formula H3, Y ¹ is —S—, Y ² is —N═, Y ³ is —CH═, A and L are single bonds, A compound in which J is a group represented by formula J1, R ⁴ , R ⁵ and R ⁶ are all methyl groups, G is a hydrogen atom, D is —CH═ and m is 0 ,
(4) Het is a group represented by the formula H4, Z ¹ is —CH═, Z ² is —N═, Z ³ is —CI═ (where I is an iodine atom, A) and L are single bonds, J is a group represented by the formula J1, R ¹ and R ² are both methyl groups, R ³ is a hydrogen atom, and G is a hydrogen atom A compound in which D is -N = and m is 0,
(5) Het is a group represented by the formula H4, Z ¹ is —N═, Z ² and Z ³ are —CH═, A and L are single bonds, and J is represented by the formula J1. R ¹ and R ² are both methyl groups, R ³ is a hydrogen atom or a methyl group, G is a hydrogen atom, D is —CH═ or —N═, a compound in which m is 0, and (6) Het is a group represented by the formula H5, Z ¹ is —N═, Z ² is —C (CH ₃ ) ═, and Z ³ is —CH═. A is —O—, L is a single bond, J is a group represented by the formula J1, R ¹ and R ² are both methyl groups, and R ³ is a hydrogen atom. A compound in which G is a hydrogen atom, D is —CH═, and m is 0. ]
The heteroaromatic ring compound shown by these. The heteroaromatic ring compound according to claim 1, wherein Het is a group represented by the formula H1. The heteroaromatic ring compound according to claim 2, wherein Y ¹ is -S- or -O-. The heteroaromatic ring compound according to claim 2, wherein Y ¹ is -S-. The heteroaromatic ring compound according to claim ¹ , wherein Het is a group represented by the formula H1, H2 or H3, and Y ¹ is -S-. The heteroaromatic ring compound according to claim 1, wherein Het is a group represented by the formula H4. Z ¹ is -N =, Z ² is -CE ¹ = and Z ³ is -CE ¹ = or -N =, or Z ¹ is -CE ¹ = and Z ² The heteroaromatic ring compound according to claim 6, wherein is -N = and Z ³ is -CE ¹ =. Z ¹ is -N = and Z ² and Z ³ are the same or different -CE ¹ =, or Z ² is -N = and Z ¹ and Z ³ are the same or different -CE The heteroaromatic ring compound according to claim 7, wherein ¹ =. The heteroaromatic ring compound according to claim 6, wherein Z ¹ and Z ³ are -N = and Z ² is -CE ¹ =. The heteroaromatic ring compound according to claim 1, wherein Het is a group represented by the formula H5. Z ¹ is -N =, Z ² is -CE ¹ = and Z ³ is -CE ¹ = or -N =, or Z ¹ is -CE ¹ = and Z ² The heteroaromatic ring compound according to claim 10, wherein is -N =, and Z ³ is -CE ¹ =. Z ¹ is -N = and Z ² and Z ³ are the same or different -CE ¹ =, or Z ² is -N = and Z ¹ and Z ³ are the same or different -CE The heteroaromatic ring compound according to claim 11, wherein ¹ =. The heteroaromatic ring compound according to claim 10, wherein Z ¹ and Z ³ are -N =, and Z ² is -CE ¹ =. A pest control agent comprising the heteroaromatic ring compound according to any one of claims 1 to 13 and an inert carrier. Use of the heteroaromatic ring compound according to any one of claims 1 to 13 for controlling pests. A method for controlling pests, comprising a step of applying an effective amount of the heteroaromatic ring compound according to any one of claims 1 to 13 to pests or habitats of pests.